The present invention relates to a class of ortho-alkyl- and ortho-alkenyl-substituted benzenesulfonamides which are useful as general or selective pre-emergent or post-emergent herbicides and plant growth regulants.
U.S. Pat. No. 4,368,069 discloses and claims a class of herbicidal sulfonamides including compounds of the following structure: ##STR1## wherein R is ##STR2## R.sub.2 can be C.sub.2 -C.sub.5 alkenyl; n is 0 or 1;
R.sub.1 can be H; PA0 X and Y can be various substituents including CH.sub.3 or OCH.sub.3 ; and PA0 Z can be CH or N. PA0 R.sub.2 is H, F, Cl, CH.sub.3, OCH.sub.3 or CF.sub.3 ; PA0 R.sub.3 is H or CH.sub.3 ; PA0 R.sub.4 is H, F, Cl, Br or CH.sub.3 ; PA0 R.sub.5 is F, Cl, Br, OC(O)R.sub.6, OC(O)CF.sub.3, OH, OCH.sub.2 .phi., OSO.sub.2 R.sub.6, OSO.sub.2 CF.sub.3, OSO.sub.2 C.sub.6 H.sub.5 R.sub.7, S(O).sub.m R.sub.6, OSO.sub.2 N(CH.sub.3).sub.2 or CO.sub.2 R.sub.8 ; PA0 R.sub.6 is C.sub.1 -C.sub.3 alkyl; PA0 R.sub.7 is H, F, Cl, Br, CH.sub.3, OCH.sub.3 or CF.sub.3 ; PA0 R.sub.8 is C.sub.1 -C.sub.3 alkyl, CH.sub.2 CH.dbd.CH.sub.2, CH.sub.2 CH.sub.2 OCH.sub.3 or CH.sub.2 CH.sub.2 Cl; PA0 R.sub.9 is OCH.sub.3 or OCH.sub.2 CH.sub.3 ; PA0 R.sub.10 is H, OCH.sub.3 or OCH.sub.2 CH.sub.3 ; PA0 R.sub.11 is H, Cl or OCH.sub.3 ; PA0 R.sub.12 is H or CH.sub.3 ; PA0 n is 0 or 1; PA0 m is 0, 1 or 2; PA0 A is ##STR6## X is CH.sub.3, OCH.sub.3, Cl, F, Br, CH.sub.2 CH.sub.3, OCH.sub.2 CH.sub.3 or OCF.sub.2 H; PA0 Y is H, NH.sub.2, NHCH.sub.3, N(CH.sub.3).sub.2, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkyl substituted with 1-3 atoms of (a) F, (b) Cl or (c) Br, CH.sub.2 OCH.sub.3, CH.sub.2 OCH.sub.2 CH.sub.3, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.2 alkylthio, C.sub.3 -C.sub.4 alkenyloxy, C.sub.3 -C.sub.4 alkynyloxy, OCH.sub.2 CH.sub.2 OCH.sub.3, CH(OCH.sub.3).sub.2, CH(OCH.sub.2 CH.sub.3).sub.2, ##STR7## OCH.sub.2 CF.sub.3, OCH.sub.2 CH.sub.2 F, OCH.sub.2 CH.sub.2 Cl, OCH.sub.2 CH.sub.2 Br or GCF.sub.2 T; wherein G is O or S and T is H, CHClF, CHBrF, CF.sub.2 H or CHFCF.sub.3 ; PA0 Z is CH, N, CCH.sub.3, CBr, CCl, CF or CCH.sub.2 CH.sub.3 ; PA0 X.sub.1 is O or CH.sub.2 ; PA0 Y.sub.1 is H, CH.sub.3, OCH.sub.3 or Cl; PA0 X.sub.2 is CH.sub.3, OCH.sub.3 or SCH.sub.3 ; PA0 Y.sub.2 is CH.sub.3, CH.sub.2 CH.sub.3 or CH.sub.2 CF.sub.3 ; and PA0 X.sub.3 is CH.sub.3 or OCH.sub.3 ; PA0 (a) when R.sub.4 is halogen, R.sub.5 is the same halogen; PA0 (b) when R.sub.5 is halogen, R.sub.4 is either hydrogen or the same halogen; PA0 (c) when n is 1, R.sub.11 is hydrogen; PA0 (d) when R.sub.12 is CH.sub.3 and R.sub.10 is alkoxy, R.sub.9 is the same alkoxy; and PA0 (e) when X is Cl, then Z is CH and Y is NH.sub.2, NHCH.sub.3, N(CH.sub.3).sub.2, CH.sub.3, OCH.sub.3, or OCF.sub.2 H. PA0 (1) Compounds of generic Formula I wherein PA0 (3) Compounds of Preferred 2 wherein PA0 N-[(4,6-dimethoxy-1,3,5-triazin-2-yl)aminocarbonyl]aminosulfonyl-2-(2-metho xyethyl)benzenesulfonamide; PA0 N-[(4-methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]aminosulfonyl-2-(2-metho xyethyl)benzenesulfonamide; PA0 N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]aminosulfonyl-2-(2-p-toluenes ulfonyloxyethyl)benzenesulfonamide; PA0 N-[(4-methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]aminosulfonyl-2-(2-p-tol uenesulfonyloxyethyl)benzenesulfonamide; PA0 N-[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)aminocarbonyl]aminosulfonyl-2-(2- p-toluenesulfonyloxyethyl)benzenesulfonamide; PA0 N-[(4-methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]aminosulfonyl-2-(2-chlor oethyl)benzenesulfonamide; PA0 N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]aminosulfonyl-2-(2-chloroethy l)benzenesulfonamide; and PA0 N-[(4,6-dimethoxy-1,3,5-triazin-2-yl)aminocarbonyl]aminosulfonyl-2-(2-chlor oethyl)benzenesulfonamide. PA0 R.sub.4 is H or CH.sub.3. PA0 R.sub.4 is H or CH.sub.3. ##STR18## wherein R.sub.2 is H, F, Cl, CH.sub.3, OCH.sub.3 or CF.sub.3 ; PA0 R.sub.9 is OCH.sub.3 or OC.sub.2 H.sub.5 ; and PA0 R.sub.12 is H or CH.sub.3. ##STR19## wherein R.sub.2 is H, F, Cl, CH.sub.3, OCH.sub.3 or CF.sub.3 ; PA0 R.sub.4 is H or CH.sub.3 ; PA0 R.sub.5 is OC(O)R.sub.6, OC(O)CF.sub.3, OSO.sub.2 R.sub.6, OSO.sub.2 CF.sub.3, OSO.sub.2 C.sub.6 H.sub.4 R.sub.7, OCH.sub.2 Ph or OSO.sub.2 N(CH.sub.3).sub.2 ; and PA0 R.sub.6 and R.sub.7 are as previously defined. ##STR20## wherein R.sub.2 is H, F, Cl, CH.sub.3, OCH.sub.3 or CF.sub.3 ; PA0 R.sub.4 is H or CH.sub.3 ; and PA0 R.sub.5 is F, Cl or Br. ##STR21## wherein R.sub.2 is as previously defined; PA0 R.sub.4 is H or CH.sub.3 ; PA0 R.sub.5 is OH, F, Cl, Br, OC(O)R.sub.6, OC(O)CF.sub.3, OSO.sub.2 R.sub.6, OSO.sub.2 CF.sub.3, OSO.sub.2 C.sub.6 H.sub.4 R.sub.7, OCH.sub.2 Ph or OSO.sub.2 N(CH.sub.3).sub.2 ; and PA0 R.sub.6 and R.sub.7 are as previously defined. ##STR22## wherein R.sub.2, R.sub.9, R.sub.12, and n are as defined in the Summary of the Invention. PA0 W. E. Truce and M. F. Amos, J. Am. Chem. Soc., 73, 3013 (1951) PA0 S. J. Shafer and W. D. Clossen, J. Org. Chem., 40, 889 (1975) PA0 D. Hellwinkel and M. Supp. Tetrahedron Lett., 1499 (1975) PA0 H. W. Gschwend and H. R. Rodriquez, Organic Reactions, 26, 1 (1979). PA0 R.sub.4 is H or CH.sub.3 ; and PA0 n is 0 or 1. PA0 R.sub.10 is OCH.sub.3 or OC.sub.2 H.sub.5. PA0 R.sub.11 is Cl. PA0 R.sub.11 is OCH.sub.3. PA0 R.sub.11 is Cl. PA0 R.sub.11 is OCH.sub.3. PA0 n is 1. PA0 R.sub.2 and n are as previously defined. PA0 R.sub.4 =R.sub.5 =F, Cl, or Br. PA0 R.sub.4 is H or CH.sub.3. PA0 R.sub.4 is H or CH.sub.3. PA0 R.sub.4 is H or CH.sub.3 ; and PA0 R.sub.8 is C.sub.2 -C.sub.3 alkyl, CH.sub.2 CH.dbd.CH.sub.2, CH.sub.2 CH.sub.2 OCH.sub.3 or CH.sub.2 CH.sub.2 Cl. PA0 R.sub.4 is H or CH.sub.3. PA0 R.sub.4 is H or CH.sub.3. PA0 Y is CH(OCH.sub.3).sub.2 or ##STR56## PA0 Y is CH(OCH.sub.3).sub.2 or ##STR58## wherein X and Y are as defined in Equation 39. PA0 Z is CH or N. PA0 R.sub.3 is CH.sub.3.
European Patent Application No. 81303176.2 (Publication Number 0 044 209) discloses and claims a large number of o-benzyl-substituted sulfonamides including the following: ##STR3## These compounds are useful as plant growth regulants and as herbicides.